Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 2.2.1.12 extracted from

  • Dresen, C.; Richter, M.; Pohl, M.; Lüdeke, S.; Müller, M.
    The enzymatic asymmetric conjugate umpolung reaction (2010), Angew. Chem. Int. Ed. Engl., 49, 6600-6603.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
the gene is cloned the gene with an attached hexahistidine (His6) tag at the C terminus Serratia marcescens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
pyruvate + (E)-oct-2-enal Serratia marcescens first step in the biosynthesis of the red pigment, prodigiosin (S)-3-acetyloctanal + CO2
-
?

Organism

Organism UniProt Comment Textmining
Serratia marcescens Q5W251
-
-

Purification (Commentary)

Purification (Comment) Organism
-
Serratia marcescens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-oxobutanoate + (3E)-4-(4-chlorophenyl)but-3-en-2-one
-
Serratia marcescens ?
-
?
additional information PigD catalyzes 1,2-additions using 2-oxoacids as donor substrates and aldehydes as acceptors. In the case of ketones as acceptors PigD catalyzes the 1,4-addition. Although pyruvate is the preferred donor substrate, 2-oxobutanoate is also employed using (E)-4-(4-chlorophenyl)-but-3-en-2-one as an acceptor Serratia marcescens ?
-
?
pyruvate + (2E)-1,3-diphenylprop-2-en-1-one the PigD-catalyzed reaction yields 3% 1,4-carboligation product, with an enantiomeric excess above 99% Serratia marcescens (3R)-1,3-diphenylpentane-1,4-dione + CO2
-
?
pyruvate + (2E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one the PigD-catalyzed reaction yields 39% 1,4-carboligation product, with an enantiomeric excess above 99% Serratia marcescens (3R)-3-(2-hydroxyphenyl)-1-phenylpentane-1,4-dione + CO2
-
?
pyruvate + (2E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
-
Serratia marcescens (3R)-3-(4-methoxyphenyl)-1-phenylpentane-1,4-dione + CO2
-
?
pyruvate + (3E)-4-(4-chlorophenyl)but-3-en-2-one the PigD-catalyzed reaction yields 13% 1,4-carboligation product, with an enantiomeric excess above 99% Serratia marcescens (3R)-3-(4-chlorophenyl)hexane-2,5-dione + CO2
-
?
pyruvate + (3E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
-
Serratia marcescens (3R)-3-(4-hydroxy-3-methoxyphenyl)hexane-2,5-dione + CO2
-
?
pyruvate + (3E)-4-(furan-2-yl)but-3-en-2-one 10% conversion Serratia marcescens (3R)-3-(furan-2-yl)hexane-2,5-dione + CO2
-
?
pyruvate + (3E)-4-(thiophen-2-yl)but-3-en-2-one 15% conversion Serratia marcescens (3S)-3-(thiophen-2-yl)hexane-2,5-dione + CO2
-
?
pyruvate + (3E)-4-phenylbut-3-en-2-one the PigD-catalyzed reaction yields 7% 1,4-carboligation product, with an enantiomeric excess above 95% Serratia marcescens (3R)-3-phenylhexane-2,5-dione + CO2
-
?
pyruvate + (3E)-dec-3-en-2-one the PigD-catalyzed reaction yields 30% 1,4-carboligation product, with an enantiomeric excess above 99% Serratia marcescens (3S)-3-hexylhexane-2,5-dione + CO2
-
?
pyruvate + (3E)-non-3-en-2-one the PigD-catalyzed reaction yields 38% 1,4-carboligation product, with an enantiomeric excess above 99% Serratia marcescens (3S)-3-pentylhexane-2,5-dione + CO2
-
?
pyruvate + (E)-oct-2-enal
-
Serratia marcescens (S)-3-acetyloctanal + CO2
-
?
pyruvate + (E)-oct-2-enal first step in the biosynthesis of the red pigment, prodigiosin Serratia marcescens (S)-3-acetyloctanal + CO2
-
?
pyruvate + 3-phenylbut-3-en-2-one
-
Serratia marcescens (3R)-3-phenylhexane-2,5-dione + CO2
-
?
pyruvate + S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate highest conversion of all tested substrates into the 1,4-addition product Serratia marcescens S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate + CO2
-
?

Synonyms

Synonyms Comment Organism
pigD
-
Serratia marcescens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Serratia marcescens

Cofactor

Cofactor Comment Organism Structure
thiamine diphosphate required Serratia marcescens